Incorporation of labile trans-4,5-difluoromethanoproline into a peptide as a stable label for 19F NMR structure analysis

Мова статті: 
Англійська
Автор(и) статті: 
Kubyshkin Vladimir S. Mykhailiuk Pavel K. Afonin Sergii - Grage Stephan L. Komarov Igor V. Ulrich Anne S.
Вихідні данні статті: 
Journal of Fluorine Chemistry Volume 152, August 2013, Pages 136–143
Назва журналу: 
Journal of Fluorine Chemistry
Рік публікації: 
2013
Volume: 
152
Issue: 
Special issue: Valencia Fluorine Days, 2012
Ключові слова: 
Peptides; Amino acids; Solid state NMR; Cyclopropanation; Proline; Fluorine NMR
Ключове слово: 
peptides
Ключове слово: 
amino acids
Trans-4,5-Difluoromethano-proline was incorporated into the cyclic antimicrobial peptide gramicidin S in place of a native proline residue. Introduction of this intrinsically unstable amino acid into the polypeptide backbone was achieved using a dipeptide strategy. The stable dipeptide building block with the N-acylated 4,5-difluoromethano-proline fragment was obtained by direct difluorocyclopropanation of an unsaturated precursor. The influence of the unnatural amino acid on the conformation and function of gramicidin S was evaluated using circular dichroism and biological assays. The application of trans-4,5-difluoromethano-proline as a new label for solid state 19F NMR structure analysis of membrane-active peptides was tested on gramicidin S and compared with previous labeling schemes.
Назва підрозділу: 
Кафедра супрамолекулярної хімії та біохімії
ІНСТИТУТ ВИСОКИХ ТЕХНОЛОГІЙ Матеріали дозволено використовувати на умовах GNU FDL без незмінюваних секцій та Creative Commons Attribution/Share-Alike
Дизайн: Інститут високих технологій
Ivan Ivanov